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Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera)

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Lipids

Abstract

The present work characterizes novel FA in the royal jelly of honeybees (Apis mellifera). TLC analysis showed that the chloroform/methanol extract obtained from royal jelly consists mainly of FA. The FABMS spectrum of this extract gave several ion peaks due to compounds with higher M.W. than those of the FA so far reported. The methanol extract was found to contain unknown phospholipids. By means of reversed-phase HPLC with various solvent systems, 13 compounds were obtained in pure state. Their structures including absolute configurations were determined by chemical, NMR, and MS spectral analysis. Six compounds were identified as novel mono- or diesters of 10-hydroxy-2E-decenoic acid in which the hydroxyl group was esterified by another FA unit, and one was hydroxy-2E-decenoic acid 10-phosphate. In addition, we demonstrated that 9-hydroxy-2E-decenoic acid exists as a mixture of optical isomers.

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Abbreviations

HDA:

hydroxy-2E-decenoic acid

HMBC:

2-D heteronuclear multiple-bond correlation

MTPA:

2-methoxy-2-trifluoromethylphenylacetate

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Authors and Affiliations

  1. Institute for Health Science, Yamada Apiculture Center, Inc., 708-0393, Okayama, Japan

    Kaori Ishiyama

  2. Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, 573-0101, Osaka, Japan

    Naoki Noda, Kazue Umebayashi, Takafumi Nakatani & Kazumoto Miyahara

Authors
  1. Naoki Noda
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  2. Kazue Umebayashi
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  3. Takafumi Nakatani
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  4. Kazumoto Miyahara
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  5. Kaori Ishiyama
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Correspondence to Naoki Noda.

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Noda, N., Umebayashi, K., Nakatani, T. et al. Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera). Lipids 40, 833–838 (2005). https://doi.org/10.1007/s11745-005-1445-6

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  • DOI: https://doi.org/10.1007/s11745-005-1445-6

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